Phenylcarbamates, their preparation, and compositions comprising them

ABSTRACT

Phenylcarbamates of the formula I                    
     where: 
     R 1  is C 1 -C 4 -alkyl; 
     R 2  is cyano, nitro, trifluoromethyl, halogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; 
     m is 0, 1 or 2, where the radicals R 2  may be different if m is 2; 
     R 3  is hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl; 
     R 4 , R 5  and R 6  are each as defined in claim 1, 
     and salts thereof, a process and intermediates for preparing these compounds and compositions comprising them for controlling animal pests and harmful fungi are described.

The present invention relates to phenylcarbamates of the formula I

where:

R¹ is C₁-C₄-alkyl;

R² is cyano, nitro, trifluoromethyl, halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy;

m is 0, 1 or 2, where the radicals R² may be different if m is 2;

R³ is hydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl;

R⁴, R⁶ independently of one another are each hydrogen,

C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₁₀-alkenyl, C₂C₁₀-alkynyl, C₁-C₁₀-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₃-C₁₀-alkynylcarbonyl or C₁-C₁₀-alkylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the cyclic groups for their part may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkyloxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR⁷)—A_(n)—R⁸;

aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkyloxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR⁷)—A_(n)—R⁸;

R⁵ is hydrogen,

C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, where the hydrocarbon radicals of these groups may be partially or fully halogenated or may carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C₁-C₄-alkoxy, arylthio, aryl-C₁-C₄-alkylthio, hetaryl, hetaryloxy, hetaryl-C₁-C₄-alkoxy, hetarylthio, hetaryl-C₁-C₄-alkylthio, where the cyclic radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR⁷)—A_(n)—R⁸;

C₃-C₆-CyCloalkyl, C₃-C₆-CyCloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;

where

A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C₁-C₆-alkyl;

n is 0 or 1;

R⁷ is hydrogen or C₁-C₆-alkyl and

R⁸ is hydrogen or C₁-C₆-alkyl,

and salts thereof.

Furthermore, the invention relates to processes and intermediates for preparing these compounds and to compositions comprising them for controlling animal pests and harmful fungi.

Phenylcarbamates having a methoximino group in the ortho position are disclosed in WO-A 93/15046. α-Phenylacrylic acid and α-phenyl-α-methoximinoacetic acid derivatives having a methoximino group in the ortho position are known from EP-A 426 460, EP-A 460 575, EP-A 472 300, EP-A 585 751, WO-A 92/13830, WO-A 92/18487, WO-A 92/18494, JP-A 05/201 946 and JP-A 05/255 012. The compounds described therein carry a CH₂O—N═CR′R″ group in the position ortho to the group corresponding to the carbamate substituent.

WO-A 97/15552 discloses those α-phenylacrylic acid and α-phenyl-α-methoximinoacetic acid derivatives in which the CH₂O—N═CR′R″ group carries cyano, alkyl, haloalkyl and cycloalkyl, and bisoxime ether groups, as substituents R′ and R″, respectively.

The compounds described in the abovementioned applications are suitable for use as crop protection agents against harmful fungi and in some cases against animal pests.

It is an object of the present invention to provide novel compounds having improved activity.

We have found that this object is achieved by the phenylcarbamates I defined at the outset. Additionally, we have found processes and intermediates for their preparation, and compositions comprising them for controlling animal pests and harmful fungi, and their use to this end.

The compounds I can be obtained by various routes according to processes known per se from the literature.

In principle, when synthesizing the compounds I it is immaterial whether the carbamate group —N(OCH₃)—COOR¹ or the group

is synthesized first.

The synthesis of the carbamate group —N(OCH₃)—COOR¹ is known, for example, from WO-A 93/15046.

1. The compounds of the formula I are generally synthesized by reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III.

In the formula II, L¹ is a nucleophilically replaceable leaving group, for example halogen or a sulfonate group, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, for example sodium hydride, potassium hydroxide, potassium carbonate and triethylamine, in accordance with the methods described in Houben-Weyl, Vol. E 14b, p. 370f. and Houben-Weyl, Vol. 10/1, p. 1189f.

The required hydroxyimines III are obtained, for example, as described in Scheme 1 by a sequence of nitrosation, alkylation and oximation reactions, from the corresponding carbonyl compounds XIV.

By basic or acidic catalysis, the α-ketooxime XV can be prepared from the ketone XIV using an organic nitrite, in accordance with the methods described in Houben-Weyl, Vol. 10/4, p. 17f.

The required ketooxime ether XVII is obtained, for example, by reaction of XV with a nucleophilically substituted reagent XVI.

In the formula XVI, L¹ is a nucleophilically replaceable leaving group, for example halogen or a sulfonate group, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, for example potassium carbonate, potassium hydroxide, sodium hydride, triethylamine and pyridine, in accordance with the methods described in Houben-Weyl, Vol. 14b, p. 307f., p. 370f., and p. 385f.; Houben-Weyl Vol. 10/4, p. 55f., p. 180f., and p. 217f.; Houben-Weyl Vol. E5, p. 780f.

By basic or acidic catalysis, the α-ketooxime IV can be prepared from the ketone XVII, using an organic nitrite in accordance with the methods described in Houben-Weyl Vol. 10/4, p. 17f.

The required hydroxyimine III is obtained, for example, by reacting an appropriate α-ketooxime IV with an oxyamine XVIIIa or its salt XVIIIb. In the formula XVIIIb, Q^(⊖) is the anion of an acid, in particular an inorganic acid, for example a halide, such as chloride.

The reaction is carried out in a manner known per se in an inert organic solvent, in accordance with the methods described in EP-A 513 580; Houben-Weyl Vol. 10/4 p. 73f.; Houben-Weyl Vol. E14b p. 369f. and p. 385f.

1.1 Alternatively, the compounds I can also be obtained by initially reacting the benzyl derivative II with the carbonylhydroxyimino derivative IV to give a corresponding benzyloxyimine of the formula V, which is subsequently reacted with the hydroxylamine VIa or its salt VIb to give I.

The reaction is carried out in a manner known per se in an inert organic solvent, in accordance with the methods described in Houben-Weyl, Vol. E 14b, p. 369f.; Houben-Weyl, Vol. 10/1, p. 1189f. and Houben-Weyl, Vol. 10/4, p. 73f. or EP-A 513 580.

1.2 A further route for preparing the compounds I is the reaction of the benzyl derivative II with N-hydroxyphthalimide and subsequent hydrazinolysis to give the benzylhydroxylamine IIa, followed by reaction of IIa with a carbonyl compound VII.

The compounds II are known (WO-A 93/15046) or can be prepared by the methods described therein.

Owing to their C═C and C═N double bonds, the compounds I can be obtained in the preparation as E/Z isomer mixtures which can be separated into the individual compounds in a customary manner for example by crystallization or chromatography.

However, if isomer mixtures are obtained in the synthesis, the separation is generally not necessarily required since in some cases the individual isomers can be converted into each other during preparation for use or upon use (for example under the influence of light, acids or bases). Corresponding conversions may also occur after the application, for example in the treatment of plants in the treated plant or in the harmful fungi or animal pest to be controlled.

With regard to the —C(R³)═NOCH₂═ double bond, preference is given to the cis isomers of the compounds I with respect to their activity (configuration based on the radical R³ in relation to the —OCH₂— group).

In the definitions of the compounds I given at the outset, collective terms were used which generally represent the following groups:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms, for example C₁-C₆-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

Haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example C₁-C₂-haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

Cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon ring members, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

Alkenyl: straight-chain or branched alkenyl groups having 2 to 6 or 10 carbon atoms and a double bond in any position, for example C₂-C₆-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

Alkynyl: straight-chain or branched alkynyl groups having 2 to 10 carbon atoms and a triple bond in any position, for example C₂-C₆-alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclylamino: three- to six-membered saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur and which are attached to the skeleton either directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as, for example, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thia-diazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,3-dithian-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 1,3-dihydrooxazin-2-yl, 2H-1,4-benzoxazin-3-yl;

Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which are attached to the skeleton either directly or (aryloxy) via an oxygen atom (—O—) or (arylthio) a sulfur atom (—S—), (arylcarbonyl) via a carbonyl group (—CO—) or (arylsulfonyl) via a sulfonyl group (—SO₂—), for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;

Hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, may additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which are attached to the skeleton either directly or (hetaryloxy) via an oxygen atom (—O—) or (hetarylthio) a sulfur atom (—S—), (hetarylcarbonyl) via a carbonyl group (—CO—) or (hetarylsulfonyl) via a sulfonyl group (—SO₂—), for example

5-membered hetaryl, containing one to three nitrogen atoms: 5-membered hetaryl groups which may, in addition to carbon atoms, contain one to three nitrogen atoms as ring members, for example 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;

5-membered hetaryl, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-membered hetaryl groups which may, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 20 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl;

benzo-fused 5-membered hetaryl, containing one to three nitrogen atoms or one nitrogen atom and/or one oxygen or sulfur atom: 5-membered hetaryl groups which may, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom as ring members, and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group;

5-membered hetaryl which is attached via nitrogen and contains one to four nitrogen atoms, or benzo-fused 5-membered hetaryl which is attached via nitrogen and contains one to three nitrogen atoms: 5-membered hetaryl groups which may, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group, where these rings are attached to the skeleton via one of the nitrogen ring members;

6-membered hetaryl, containing one to three or one to four nitrogen atoms: 6-membered hetaryl groups which may, in addition to carbon atoms, contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;

benzo-fused 6-membered hetaryl, containing one to four nitrogen atoms: 6-membered hetaryl groups in which two adjacent carbon ring members may be bridged by a buta-1,3-diene-1,4-diyl group, for example quinoline, isoquinoline, quinazoline and quinoxaline,

or the corresponding oxy, thio, carbonyl or sulfonyl groups.

Hetarylamino: aromatic mono- or polycyclic radicals which may, in addition to carbon ring members, additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are attached to the skeleton via a nitrogen atom.

The term “partially or fully halogenated” is meant to express that the hydrogen atoms in the groups which are characterized in such a way may be partially or fully replaced by identical or different halogen atoms as mentioned above.

With regard to their biological activity, preference is given to compounds of the formula I in which m is 0.

Likewise, preference is given to compounds of the formula I in which R¹ is methyl.

In addition, preference is given to compounds I in which R³ is hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF₃.

Moreover, preference is given to compounds I in which R³ is methyl.

In addition, preference is given to compounds I in which R³ is cyano.

Furthermore, preference is given to compounds I in which R³ is cyclopropyl.

Furthermore, preference is given to compounds I in which R³ is CF₃.

Furthermore, preference is given to compounds I in which R⁵ is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, unsubstituted or substituted aryl or hetaryl.

Moreover, preference is given to compounds I in which R⁵ is methyl.

Furthermore, preference is given to compounds I in which R⁵ is ethyl.

Moreover, preference is given to compounds I in which R⁵ is isopropyl.

Moreover, preference is given to compounds I in which R⁵ is cyclopropyl.

Moreover, preference is given to compounds I in which r⁵ is CF₃

Furthermore, preference is given to compounds I in which R⁵ is unsubstituted or substituted aryl or hetaryl.

Furthermore, preference is given to compounds I in which R⁵ is unsubstituted or substituted pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.

Furthermore, preference is given to compounds I in which R⁵ is unsubstituted or substituted furyl, thienyl or pyrrolyl.

Furthermore, preference is given to compounds I in which R⁵ is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.

Furthermore, preference is given to compounds I in which R⁵ is unsubstituted or substituted oxadiazolyl, thiadiazolyl or triazolyl.

Moreover, preference is given to compounds I in which R⁵ is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl or di-C₁-C₄-alkylaminocarbonyl.

Moreover, preference is given to compounds I in which R⁴ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.

Furthermore, preference is given to compounds I in which R⁴ is C₁-C₆-alkyl.

Moreover, preference is given to compounds I in which R⁴ is methyl, ethyl, 2-propenyl or 2-propynyl.

Furthermore, preference is given to compounds of the formula I in which R⁶ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, arylalkyl, hetarylalkyl, aryloxyalkyl or hetaryloxyalkyl.

Moreover, preference is given to compounds I in which R⁶ is methyl, ethyl or propargyl.

Furthermore, preference is given to those compounds I in which R⁶ is arylalkyl or hetarylalkyl.

Moreover, preference is given to those compounds I in which R⁶ is aryloxyalkyl or hetaryloxyalkyl.

Furthermore, preference is given to compounds of the formula I in which the substituents are selected from a combination of the preferred substituents described above.

With respect to their use, particular preference is given to the compounds of the formula I.1 compiled in the tables below:

Table 1:

Compounds of the formula I.1, in which R³=methyl, R⁴=methyl and R⁵=hydrogen and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 2:

Compounds of the formula I.1, in which R³=methyl, R⁴=methyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 3:

Compounds of the formula I.1, in which R³=methyl, R⁴=methyl and R⁵=ethyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 4:

Compounds of the formula I.1, in which R³=methyl, R⁴=methyl and R⁵=n-propyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 5:

Compounds of the formula I.1, in which R³=methyl, R⁴=methyl and R⁵=i-propyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 6:

Compounds of the formula I.1, in which R³=methyl, R⁴=methyl and R⁵=cyclopropyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 7:

Compounds of the formula I.1, in which R³=methyl, R⁴=methyl and R⁵=cyano and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 8:

Compounds of the formula I.1, in which R³=methyl, R⁴=ethyl and R⁵=hydrogen and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 9:

Compounds of the formula I.1, in which R³=methyl, R⁴=ethyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 10:

Compounds of the formula 1.1, in which R³=methyl, R⁴=ethyl and R⁵=ethyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 11:

Compounds of the formula I.1, in which R³=methyl, R⁴=ethyl and R⁵=n-propyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 12:

Compounds of the formula I.1, in which R³=methyl, R⁴=ethyl and R⁵=i-propyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 13:

Compounds of the formula I.1, in which R³=methyl, R⁴=ethyl and R⁵=cyclopropyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 14:

Compounds of the formula I.1, in which R³=methyl, R⁴=ethyl and R⁵=cyano and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 15:

Compounds of the formula I.1, in which R³=methyl, R⁴=propargyl and R⁵=hydrogen and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 16:

Compounds of the formula I.1, in which R³=methyl, R⁴=propargyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 17:

Compounds of the formula I.1, in which R³=methyl, R⁴=propargyl and R⁵=ethyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 18:

Compounds of the formula I.1, in which R³=methyl, R⁴=propargyl and R⁵=n-propyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 19:

Compounds of the formula I.1, in which R³=methyl, R⁴=propargyl and R⁵=i-propyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 20:

Compounds of the formula I.1, in which R³=methyl, R⁴=propargyl and R⁵=cyclopropyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 21:

Compounds of the formula I.1, in which R³=methyl, R⁴=propargyl and R⁵=cyano and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 22:

Compounds of the formula I.1, in which R³=trifluoromethyl, R⁴ =methyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 23:

Compounds of the formula I.1, in which R³=trifluoromethyl, R⁴=ethyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 24:

Compounds of the formula I.1, in which R³=trifluoromethyl, R⁴=propargyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 25:

Compounds of the formula I.1, in which R³=cyclopropyl, R⁴=methyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 26:

Compounds of the formula I.1, in which R³=cyclopropyl, R⁴=ethyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 27:

Compounds of the formula I.1, in which R³=cyclopropyl, R⁴=propargyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 28:

Compounds of the formula I.1, in which R³=cyano, R⁴=methyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 29:

Compounds of the formula I.1, in which R³=cyano, R⁴=ethyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

Table 30:

Compounds of the formula I.1, in which R³=cyano, R⁴=propargyl and R⁵=methyl and the substituent R⁶ corresponds for each compound to one line of Table A.

TABLE A No. R⁶ 1 H 2 CH₃ 3 CH₂CH₃ 4 CH₂CH₂CH₃ 5 CH(CH₃)₂ 6 cyclopropyl 7 (CH₂)₃CH₃ 8 CH(CH₃)CH₂CH₃ 9 CH₂CH(CH₃)₂ 10 C(CH₃)₃ 11 cyclobutyl 12 (CH₂)₄CH₃ 13 CH(CH₃)(CH₂)₂CH₃ 14 CH₂CH(CH₃)CH₂CH₃ 15 (CH₂)₂CH(CH₃)₂ 16 CH₂C(CH₃)₃ 17 CH(CH₂CH₃)₂ 18 C(CH₃)₂CH₂CH₃ 19 CH(CH₃)CH(CH₃)₂ 20 cyclopentyl 21 (CH₂)₅CH₃ 22 CH(CH₃)(CH₂)₃CH₃ 23 CH(CH₂CH₃)(CH₂)₂CH₃ 24 CH₂CH(CH₃)(CH₂)₂CH₃ 25 (CH₂)₂CH(CH₃)CH₂CH₃ 26 (CH₂)₃CH(CH₃)₂ 27 (CH₂)₂C(CH₃)₃ 28 CH₂CH(CH₂CH₃)₂ 29 CH(CH₃)CH(CH₃)CH₂CH₃ 30 CH(CH₃)CH₂CH(CH₃)₂ 31 CH₂CH(CH₃)CH(CH₃)₂ 32 CH(CH₃)C(CH₃)₃ 33 CH(CH₂CH₃)CH(CH₃)₂ 34 C(CH₃)₂CH₂CH₂CH₃ 35 CH₂C(CH₃)₂CH₂CH₃ 36 C(CH₃)₂CH(CH₃)₂ 37 cyclohexyl 38 CH₂CN 39 (CH₂)₂CN 40 (CH₂)₃CN 41 (CH₂)₄CN 42 (CH₂)₂OCH₃ 43 (CH₂)₃OCH₃ 44 (CH₂)₄OCH₃ 45 (CH₂)₂OCH₂CH₃ 46 (CH₂)₃OCH₂CH₃ 47 (CH₂)₄OCH₂CH₃ 48 (CH₂)₂O(CH₂)₂CH₃ 49 (CH₂)₃O(CH₂)₂CH₃ 50 (CH₂)₄O(CH₂)₂CH₃ 51 (CH₂)₂OCH(CH₃)₂ 52 (CH₂)₃OCH(CH₃)₂ 53 (CH₂)₄OCH(CH₃)₂ 54 (CH₂)₂OC(CH₃)₃ 55 (CH₂)₃OC(CH₃)₃ 56 (CH₂)₄OC(CH₃)₃ 57 (CH₂)₂OCF₃ 58 (CH₂)₃OCF₃ 59 (CH₂)₄OCF₃ 60 (CH₂)₂SCH₃ 61 CH₃(CH₂)₃SCH₃ 62 (CH₂)₄SCH₃ 63 CH₂-cyclopropyl 64 (CH₂)₂-cyclopropyl 65 (CH₂)3-cyclopropyl 66 (CH₂)₄-cyclopropyl 67 CH₂-cyclopentyl 68 (CH₂)₂-cyclopentyl 69 (CH₂)₃-cyclopentyl 70 (CH₂)₄-cyclopentyl 71 CH₂-cyclohexyl 72 (CH₂)₂-cyclohexyl 73 (CH₂)₃-cyclohexyl 74 (CH₂)₄-cyclohexyl 75 CHF₂ 76 CF₃ 77 CH₂CHF₂ 78 CH₂CF₃ 79 CHFCHF₂ 80 CH₂CH₂F 81 CHFCH₃ 82 CHFCF₃ 83 CF₂CHF₂ 84 CF₂CHFCF₃ 85 CH₂CCl₃ 86 CF₂CHCl₂ 87 CF₂CHFCl 88 CF₂CHFBr 89 CH(CF₃)₂ 90 CH(CF₃)CH₃ 91 CH₂CH₂CF₃ 92 CH₂CHFCH₃ 93 CH₂CF₂CF₃ 94 CH₂CH₂CH₂F 95 CH₂CF₂CF₂CF₃ 96 CH₂CH₂CHFCH₃ 97 CH₂CH₂CH₂CH₂F 98 CH₂CH₂Cl 99 CH₂CHClCH₃ 100 CH₂CH₂CH₂Cl 101 CH₂CH₂CHClCH₃ 102 CH₂CH₂CH₂CH₂Cl 103 CH₂CH₂Br 104 CH₂CHBrCH₃ 105 CH₂CH₂CH₂Br 106 CH₂CH₂CHBrCH₃ 107 CH₂CH₂CH₂CH₂Br 108 CH₂—C₆H₅ 109 CH(CH₃)CN 110 CH(CH₃)CH₂CN 111 CH₂CH(CH₃)CN 112 CH(CH₃)CH(CH₃)CN 113 CH(CH₃)(CH₂)₂CN 114 CH₂CH(CH₃)CH₂CN 115 (CH₂)₂CH(CH₃)CN 116 CH(CH₃)CH(CH₃)CH₂CN 117 CH(CH₃)CH₂CH(CH₃)CN 118 CH₂CH(CH₃)CH(CH₃)CN 119 CH(CH₃)CH(CH₃)CH(CH₃)CN 120 CH(CH₃)(CH₂)₃CN 121 CH(CH₃)CH₂OH 122 CH₂CH(CH₃)OH 123 CH(CH₃)CH(CH₃)OH 124 CH(CH₃)(CH₂)₂0H 125 CH₂CH(CH₃)CH₂OH 126 (CH₂)₂CH(CH₃)OH 127 CH(CH₃)CH(CH₃)CH₂OH 128 CH(CH₃)CH₂CH(CH₃)OH 129 CH₂CH(CH₃)CH(CH₃)OH 130 CH(CH₃)CH(CH₃)CH(CH₃)OH 131 CH(CH₃)(CH₂)₃OH 132 CH(CH₃)CH₂OCH₃ 133 CH₂CH(CH₃)OCH₃ 134 CH(CH₃)CH(CH₃)OCH₃ 135 CH(CH₃)(CH₂)₂OCH₃ 136 CH₂CH(CH₃)CH₂OCH₃ 137 (CH₂)₂CH(CH₃)OCH₃ 138 CH(CH₃)CH(CH₃)CH₂OCH₃ 139 CH(CH₃)CH₂CH(CH₃)OCH₃ 140 CH₂CH(CH₃)CH(CH₃)OCH₃ 141 CH(CH₃)CH(CH₃)CH(CH₃)OCH₃ 142 CH(CH₃)(CH₂)₃OCH₃ 143 CH(CH₃)CH₂OCH₂CH₃ 144 CH₂CH(CH₃)OCH₂CH₃ 145 CH(CH₃)CH(CH₃)OCH₂CH₃ 146 CH(CH₃)(CH₂)₂OCH₂CH₃ 147 CH₂CH(CH₃)CH₂OCH₂CH₃ 148 (CH₂)₂CH(CH₃)OCH₂CH₃ 149 CH(CH₃)CH(CH₃)CH₂OCH₂CH₃ 150 CH(CH₃)CH₂CH(CH₃)OCH₂CH₃ 151 CH₂CH(CH₃)CH(CH₃)OCH₂CH₃ 152 CH(CH₃)CH(CH₃)CH(CH₃)OCH₂CH₃ 153 CH(CH₃)(CH₂)₃OCH₂CH₃ 154 CH(CH₃)CH₂O(CH₂)₂CH₃ 155 CH₂CH(CH₃)O(CH₂)₂CH₃ 156 CH(CH₃)CH(CH₃)O(CH₂)₂CH₃ 157 CH(CH₃)(CH₂)₂0(CH₂)₂CH₃ 158 CH₂CH(CH₃)CH₂O(CH₂)₂CH₃ 159 (CH₂)₂CH(CH₃)O(CH₂)₂CH₃ 160 CH(CH₃)CH(CH₃)CH₂O(CH₂)₂CH₃ 161 CH(CH₃)CH₂CH(CH₃)O(CH₂)₂CH₃ 162 CH₂CH(CH₃)CH(CH₃)O(CH₂)₂CH₃ 163 CH(CH₃)CH(CH₃)CH(CH₃)O(CH₂)₂CH₃ 164 CH(CH₃)(CH₂)₃O(CH₂)₂CH₃ 165 CH(CH₃)CH₂OCH(CH₃)₂ 166 CH₂CH(CH₃)OCH(CH₃)₂ 167 CH(CH₃)CH(CH₃)OCH(CH₃)₂ 168 CH(CH₃)(CH₂)₂OCH(CH₃)₂ 169 CH₂CH(CH₃)CH₂OCH(CH₃)₂ 170 (CH₂)₂CH(CH₃)OCH(CH₃)₂ 171 CH(CH₃)CH(CH₃)CH₂OCH(CH₃)₂ 172 CH(CH₃)CH₂CH(CH₃)OCH(CH₃)₂ 173 CH₂CH(CH₃)CH(CH₃)OCH(CH₃)₂ 174 CH(CH₃)CH(CH₃)CH(CH₃)OCH(CH₃)₂ 175 CH(CH₃)(CH₂)₃OCH(CH₃)₂ 176 CH(CH₃)CH₂OC(CH₃)₃ 177 CH₂CH(CH₃)OC(CH₃)₃ 178 CH(CH₃)CH(CH₃)OC(CH₃)₃ 179 CH(CH₃)(CH₂)₂OC(CH₃)₃ 180 CH₂CH(CH₃)CH₂OC(CH₃)₃ 181 (CH₂)₂CH(CH₃)OC(CH₃)₃ 182 CH(CH₃)CH(CH₃)CH₂OC(CH₃)₃ 183 CH(CH₃)CH₂CH(CH₃)OC(CH₃)₃ 184 CH₂CH(CH₃)CH(CH₃)OC(CH₃)₃ 185 CH(CH₃)CH(CH₃)CH(CH₃)OC(CH₃)₃ 186 CH(CH₃)(CH₂)₃OC(CH₃)₃ 187 CH(CH₃)CH₂OCF₃ 188 CH₂CH(CH₃)OCF₃ 189 CH(CH₃)CH(CH₃)OCF₃ 190 CH(CH₃)(CH₂)₂OCF₃ 191 CH₂CH(CH₃)CH₂OCF₃ 192 (CH₂)₂CH(CH₃)OCF₃ 193 CH(CH₃)CH(CH₃)CH₂OCF₃ 194 CH(CH₃)CH₂CH(CH₃)OCF₃ 195 CH₂CH(CH₃)CH(CH₃)OCF₃ 196 CH(CH₃)CH(CH₃)CH(CH₃)OCF₃ 197 CH(CH₃)(CH₂)₃OCF₃ 198 CH(CH₃)CH₂SCH₃ 199 CH₂CH(CH₃)SCH₃ 200 CH(CH₃)CH(CH₃)SCH₃ 201 CH(CH₃)(CH₂)₂SCH₃ 202 CH₂CH(CH₃)CH₂SCH₃ 203 (CH₂)₂CH(CH₃)SCH₃ 204 CH(CH₃)CH(CH₃)CH₂SCH₃ 205 CH(CH₃)CH₂CH(CH₃)SCH₃ 206 CH₂CH(CH₃)CH(CH₃)SCH₃ 207 CH(CH₃)CH(CH₃)CH(CH₃)SCH₃ 208 CH(CH₃)(CH₂)₃SCH₃ 209 CH(CH₃)CH₂SOCH₃ 210 CH₂CH(CH₃)SOCH₃ 211 CH(CH₃)-cyclopropyl 212 CH(CH₃)CH₂-cyclopropyl 213 CH₂CH(CH₃)-cyclopropyl 214 CH(CH₃)CH(CH₃)-cyclopropyl 215 CH(CH₃)(CH₂)₂-cyclopropyl 216 CH₂CH(CH₃)CH₂-cyclopropyl 217 (CH₂)₂CH(CH₃)-cyclopropyl 218 CH(CH₃)CH(CH₃)CH₂-cyclopropyl 219 CH(CH₃)CH₂CH(CH₃)-cyclopropyl 220 CH₂CH(CH₃)CH(CH₃)-cyclopropyl 221 CH(CH₃)CH(CH₃)CH(CH₃)-cyclopropyl 222 CH(CH₃)(CH₂)3-cyclopropyl 223 CH(CH₃)-cyclopentyl 224 CH(CH₃)CH₂-cyclopentyl 225 CH₂CH(CH₃)-cyclopentyl 226 CH(CH₃)CH(CH₃)-cyclopentyl 227 CH(CH₃)(CH₂)₂-cyclopentyl 228 CH₂CH(CH₃)CH₂-cyclopentyl 229 (CH₂)₂CH(CH₃)-cyclopentyl 230 CH(CH₃)CH(CH₃)CH₂-cyclopentyl 231 CH(CH₃)CH₂CH(CH₃)-cyclopentyl 232 CH₂CH(CH₃)CH(CH₃)-cyclopentyl 233 CH(CH₃)CH(CH₃)CH(CH₃)-cyclopentyl 234 CH(CH₃)(CH₂)₃-cyclopentyl 235 CH(CH₃)-cyclohexyl 236 CH(CH₃)CH₂-cyclohexyl 237 CH₂CH(CH₃)-cyclohexyl 238 CH(CH₃)CH(CH₃)-cyclohexyl 239 CH(CH₃)(CH₂)₂-cyclohexyl 240 CH₂CH(CH₃)CH₂-cyclohexyl 241 (CH₂)₂CH(CH₃)-cyclohexyl 242 CH(CH₃)CH(CH₃)CH₂-cyclohexyl 243 CH(CH₃)CH₂CH(CH₃)-cyclohexyl 244 CH₂CH(CH₃)CH(CH₃)-cyclohexyl 245 CH(CH₃)CH(CH₃)CH(CH₃)-cyclohexyl 246 CH(CH₃)(CH₂)₃-cyclohexyl 247 CH(CH₃)CHF₂ 248 CF(CH₃)CHF₂ 249 CH(CH₃)CH₂F 250 CF(CH₃)CH₃ 251 CF(CH₃)CF₃ 252 CH(CH₃)CCl₃ 253 CH(CH₃)CH₂CF₃ 254 CH₂CH(CH₃)CF₃ 255 CH(CH₃)CH(CH₃)CF₃ 256 CH(CH₃)CF₂CF₃ 257 CH(CH₃)-phenyl 258 CH(CH₃)CH₂-phenyl 259 CH₂CH(CH₃)-phenyl 260 CH(CH₃)CH(CH₃)-phenyl 261 CH(CH₃)(CH₂)₂-phenyl 262 CH₂CH(CH₃)CH₂-phenyl 263 (CH₂)₂CH(CH₃)-phenyl 264 CH(CH₃)CH(CH₃)CH₂-phenyl 265 CH(CH₃)CH₂CH(CH₃)-phenyl 266 CH₂CH(CH₃)CH(CH₃)-phenyl 267 CH(CH₃)CH(CH₃)CH(CH₃)-phenyl 268 CH(CH₃)(CH₂)₃-phenyl 269 2-CH₃—C₆H₄—CH₂ 270 3-CH₃—C₆H₄—CH₂ 271 4-CH₃—C₆H₄—CH₂ 272 2,3-(CH₃)_(2-C) ₆H₃—CH₂ 273 2,4-(CH₃)_(2-C) ₆H₃—CH₂ 274 2,5-(CH₃)_(2-C) ₆H₃—CH₂ 275 2,6-(CH₃)_(2-C) ₆H₃—CH₂ 276 3,4-(CH₃)_(2-C) ₆H₃—CH₂ 277 3,5-(CH₃)_(2-C) ₆H₃—CH₂ 278 2-CH₂CH₃—C₆H₄—CH₂ 279 3-CH₂CH₃—C₆H₄—CH₂ 280 4-CH₂CH₃—C₆H₄—CH₂ 281 2-CH(CH₃)_(2-C) ₆H₄—CH₂ 282 3-CH(CH₃)_(2-C) ₆H₄—CH₂ 283 4-CH(CH₃)_(2-C) ₆H₄—CH₂ 284 3-C(CH₃)₃—C₆H₄—CH₂ 285 4-C(CH₃)₃—C₆H₄—CH₂ 286 2-C₆H₅—C₆H₄—CH₂ 287 3-C₆H₅—C₆H₄—CH₂ 288 4-C₆H₅—C₆H₄—CH₂ 289 2-OCH₃—C₆H₄—CH₂ 290 3-OCH₃—C₆H₄—CH₂ 291 4-OCH₃—C₆H₄—CH₂ 292 2,3-(OCH₃)₂—C₆H₃—CH₂ 293 2,4-(OCH₃)₂—C₆H₃—CH₂ 294 2,5-(OCH₃)₂—C₆H₃—CH₂ 295 2,6-(OCH₃)₂—C₆H₃—CH₂ 296 3,4-(OCH₃)₂—C₆H₃—CH₂ 297 3,5-(OCH₃)₂—C₆H₃—CH₂ 298 3,4,5-(OCH₃)₃—C₆H₂—CH₂ 299 2-OCH₂CH₃—C₆H₄—CH₂ 300 3-OCH₂CH₃—C₆H₄—CH₂ 301 4-OCH₂CH₃—C₆H₄—CH₂ 302 2-O(CH₂)₂CH₃—C₆H₄—CH₂ 303 3-O(CH₂)₂CH₃—C₆H₄—CH₂ 304 4-O(CH₂)₂CH₃—C₆H₄—CH₂ 305 2-OCH(CH₃)₂—C₆H₄—CH₂ 306 3-OCH(CH₃)₂—C₆H₄—CH₂ 307 4-OCH(CH₃)₂—C₆H₄—CH₂ 308 3-OC(CH₃)₃—C₆H₄—CH₂ 309 4-OC(CH₃)₃—C₆H₄—CH₂ 310 2-OCH₂CH═CH₂—C₆H₄—CH₂ 311 3-OCH₂CH═CH₂—C₆H₄—CH₂ 312 4-OCH₂CH═CH₂—C₆H₄—CH₂ 313 2-CF₃—C₆H₄—CH₂ 314 3-CF₃—C₆H₄—CH₂ 315 4-CF₃—C₆H₄—CH₂ 316 2-CO₂CH₃—C₆H₄—CH₂ 317 2-SCH₃—C₆H₄—CH₂ 318 3-SCH₃—C₆H₄—CH₂ 319 4-SCH₃—C₆H₄—CH₂ 320 2-OCF₃—C₆H₄—CH₂ 321 3-OCF₃—C₆H₄—CH₂ 322 4-OCF₃—C₆H₄—CH₂ 323 2-OCHF₂—C₆H₄—CH₂ 324 3-OCHF₂—C₆H₄—CH₂ 325 4-OCHF₂—C₆H₄—CH₂ 326 3-CF₃, 4-OCF₃—C₆H₃—CH₂ 327 2-CH₂CH₂F—C₆H₄—CH₂ 328 3-CH₂CH₂F—C₆H₄—CH₂ 329 4-CH₂CH₂F—C₆H₄—CH₂ 330 2-CH₂CF₃—C₆H₄—CH₂ 331 3-CH₂CF₃—C₆H₄—CH₂ 332 CH₂C≡CH 333 CH₂C≡CCl 334 CH₂C≡CBr 335 CH₂C≡CI 336 CH₂C≡CCH₃ 337 CH₂C≡CCH₂CH₃

The compounds I are suitable for use as fungicides.

The compounds I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can be employed as foliar- and soil-acting fungicides in crop protection.

They are especially important for controlling a large number of fungi on a variety of crop plants such as wheat, rye, barley, oats, rice, maize, grass, cotton, soybeans, coffee, sugar cane, grapevines, fruit species, ornamentals and vegetables such as cucumbers, beans, and cucurbits, and on the seeds of these plants.

Specifically, they are suitable for controlling the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Uncinula necator on grapevines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamentals and grapevines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on a variety of plants, Plasmopara viticola on grapevines, Alternaria species on vegetables and fruit.

Moreover, the compounds I are suitable for controlling harmful fungi in the protection of materials (eg. wood, paper, fibers or tissues) and in the protection of stored products.

The compounds I are applied by treating the fungi, or the plants, seeds, materials or the soil to be protected against fungal infection, with a fungicidally active amount of the active ingredients. Application is effected before or after infection of the materials, plants or seeds by the fungi.

They can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the specific intended use; in any case, it should guarantee fine and uniform distribution of the compound according to the invention. The formulations are prepared in a known manner, eg. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent. Suitable auxiliaries for this purpose are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispersants such as lignin-sulfite waste liquors and methylcellulose.

The fungicidal compositions generally comprise from 0.1 to 95, preferably from 0.5 to 90, % by weight of active ingredient.

Depending on the nature of the desired effect, the rates of application for use in crop protection are from 0.01 to 2.0 kg of active ingredient per ha.

In the treatment of seed, amounts of active ingredient of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram of seed.

When used in the protection of materials or stored products, the rate of application of active ingredient depends on the nature of the field of application and on the desired effect. Normal rates of application in the protection of materials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of material treated.

In the use form as fungicides, the compositions according to the invention can also exist together with other active ingredients, e.g. with herbicides, insecticides, growth regulators, fungicides, or else with fertilizers.

A mixture with fungicides frequently results in a widened fungicidal spectrum of action.

The following list of fungicides together with which the compounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation:

sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc (N,N′-propylenebisdithiocarbamate), N,N′-polypropylenebis(thiocarbamoyl) disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl 5-nitro-isophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-di-ethylphthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonyl-aminobenzimidazole, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfodiamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis-[1-(2,2,2-trichloroethyl)formamide], 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethyl-morphine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, and a variety of fungicides such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

The compounds of the formula I are furthermore suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be employed as pesticides in crop protection and in the hygiene, stored-product and veterinary sector.

The harmful insects include, from the order of the lepidopterans (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.

From the order of the dipterans (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, TipUla oleracea, TipUla paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterans (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monororium pharaonis, Solenopsis geminata, Solenopsis invicta.

From the order of the heteropterans (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, EUschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.

From the order of the homopterans (Homoptera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.

From the order of the termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.

From the order of the orthopterans (Orthoptera), for example, Acheta domestics, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example, arachnids (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.

From the class of the nematodes, for example, root knot nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem eelworms and foliar nematodes, eg. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi.

The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of ready-to-spray solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.

The concentrations of active ingredient in the ready-to-use preparations can be varied within substantial ranges.

In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients can also be used successfully in the ultra-low-volume method (ULV), it being possible to apply formulations with over 95% by weight of active ingredient, or even the active ingredient without additives.

Under field conditions, the rate of application of active ingredient for controlling pests is 0.1 to 2.0, preferably 0.2 to 1.0, kg/ha.

Substances which are suitable for the preparation of ready-to-spray solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal-tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agent, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active ingredient, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

Examples of the formulations are:

I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surface of this silica gel. This gives a preparation of the active ingredient with good adhesion (comprises 23% by weight of active ingredient).

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 9% by weight of active ingredient).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (comprises 80% by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (comprises 90% by weight of active ingredient).

VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.

Granules, eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients onto solid carriers. Examples of solid carriers are mineral earths such as silica gel, silicas, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nut shell meal, cellulose powders, and other solid carriers.

Various types of oils, or herbicides, fungicides, other pesticides, or bactericides, can be added to the active ingredients, if appropriate also only just prior to use (tank mix). These agents can be admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.

SYNTHESIS EXAMPLES

The protocols given in the synthesis examples which follow were used for obtaining further compounds I by altering the starting compounds as required. The resulting compounds are listed in Table 1 below, with physical information

EXAMPLE 1 Preparation of [I-1]

At 20-25° C., a solution of 0.95 g (0.005 mol) of 2,3,4-pentatrione 2-(E)-3-(Z)-bis(O-methyloxime) 4-(E)-oxime (cf.: DE-A 195 39 324), 2.0 g (0.006 mol) of methyl N-(2-bromomethylhenyl)-N-methoxycarbamate in 10 ml of dimethylformamide was stirred with 2.1 g (0.014 mol) of potassium carbonate for 20 hours. The reaction mixture was suspended in water and extracted with ethyl acetate. The combined organic phases were washed with sat. sodium chloride solution, dried and freed from the solvent. Silica gel chromatography (cyclohexane/ethyl acetate mixture 9:1) of the residue gave 1.4 g of the title compound as an oil.

¹H NMR (CDCl₃; δ in ppm): 1.8 (s, 3H); 2.08 (s, 3H); 3.70 (s, 3H); 3.77 (s, 3H); 3.90 (s, 3H); 3.95 (s, 3H); 5.20 (s, 2H); 7.20-7.50 (m, 4H).

TABLE I

Physical Data (IR No. R² R³ R⁴ R⁵ R⁶ [cm⁻¹], ¹H NMR: δ [ppm]) I-1 H CH₃ CH₃ CH₃ CH₃ IR: 1740, 1712, 1457, 1441, 1359, 1138, 1102, 1085, 1047, 895 I-2 H CH₃ C₂H₅ CH₃ CH₃ ¹H NMR (CDCl₃): 7,4(m, brd); 5.2(s); 4.2(q); 3.8; 3.7; 3.6(s); 2.1; 1.8(s); 1.2(t) I-3 H CH₃ C₃H₃ CH₃ CH₃ IR: 1738, 1711, 1456, 1441, 1358, 1099, 1049, 1026, 1007, 892 I-4 H CH₃ CH₃ CH₃ C₂H₅ IR: 1741, 1712, 1457, 1441, 1358, 1090, 1048, 1035, 872 I-5 H CH₃ CH₃ CH₃ CH(CH₃)₂ IR: 1742, 1713, 1456, 1441, 1369, 1359, 1343, 1328, 1030, 956 I-6 H CH₃ CH₃ CH₃ C₃H₃ IR: 1738, 1711, 1456, 1441, 1359, 1246, 1086, 1039, 1007, 884 I-7 H CH₃ C₂H₅ CH₃ C₃H₃ IR: 1739, 1711, 1456, 1441, 1357, 1093, 1040, 1007, 978, 927 I-8 H CH₃ C₃H₃ CH₃ C₃H₃ IR: 1736, 1710, 1456, 1441, 1357, 1093, 1041, 1028, 1005 I-9 H CH₃ CH₃ CH₃ C₃H₅ IR: 1741, 1712, 1457, 1441, 1360, 1246, 1100, 1085, 1031, 886  I-10 H CH₃ C₂H₅ CH₃ C₃H₅ IR: 1741, 1713, 1456, 1441, 1357, 1246, 1094, 1032, 998, 924  I-11 H CH₃ C₃H₃ CH₃ C₃H₅ IR: 1739, 1711, 1456, 1441, 1358, 1245, 1103, 1027, 1007, 923

Examples of the Activity Against Harmful Fungi

The fungicidal activity of the compounds of the formula I was demonstrated by the following experiments:

The active ingredients were formulated, separately or together, as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Wettol® EM (nonionic emulsifier based on ethoxylated castor oil) and diluted with water to the desired concentration.

The compounds compiled in the table below, known from WO-A 97/15552, were used as comparative active ingredients:

Com- parison known from No. WO-A 97/15552 Q R⁴ R⁶ A.7 Tab. 327, No. 919 C(═NOCH₃)COOCH₃ C₂H₅ C₃H₃ B.7 Tab. 328, No. 919 C(═NOCH₃)CONHCH₃ C₂H₅ C₃H₃ C.7 Tab. 325, No. 919 C(═CHOCH₃)COOCH₃ C₂H₅ C₃H₃ D.7 Tab. 326, No. 919 C(═CHCH₃)COOCH₃ C₂H₅ C₃H₃ A.8 Tab. 648, No. 919 C(═NOCH₃)COOCH₃ C₃H₃ C₃H₃ B.8 Tab. 647, No. 919 C(═NOCH₃)CONHCH₃ C₃H₃ C₃H₃ C.8 Tab. 645, No. 919 C(═CHOCH₃)COOCH₃ C₃H₃ C₃H₃ D.8 Tab. 646, No. 919 C(═CHCH₃)COOCH₃ C₃H₃ C₃H₃ A.9 Tab. 8, No. 827 C(═NOCH₃)COOCH₃ CH₃ C₃H₅ B.9 Tab. 7, No. 827 C(═NOCH₃)CONHCH₃ CH₃ C₃H₅ C.9 Tab. 5, No. 827 C(═CHOCH₃)COOCH₃ CH₃ C₃H₅ D.9 Tab. 6, No. 827 C(═CHCH₃)COOCH₃ CH₃ C₃H₅  A.11 Tab. 648, No. 827 C(═NOCH₃)COOCH₃ C₃H₃ C₃H₅  B.11 Tab. 647, No. 827 C(═NOCH₃)CONHCH₃ C₃H₃ C₃H₅  C.11 Tab. 645, No. 827 C(═CHOCH₃)COOCH₃ C₃H₃ C₃H₅  D.11 Tab. 646, No. 827 C(═CHCH₃)COOCH₃ C₃H₃ C₃H₅

Use Example 1—Curative Activity Against Puccinia recondita on Wheat (wheat leaf rust)

Leaves of potted weed seedlings of the variety “Frühgold” were dusted with spores of leaf rust (Puccinia recondita). Thereafter, the pots were kept for 24 hours in a chamber of high atmospheric humidity (90-95%), at 20-22° C. During this time, the spores germinated and the germinal tubes penetrated into the leaf tissue. The next day, the infected plants were sprayed to runoff point with an aqueous formulation of active ingredient prepared from a stock solution consisting of 10% of active ingredient, 63% of cyclohexanone and 27% of emulsifier. After the spray coating had dried on, the test plants were cultivated in a greenhouse at 20-22° C. and 65-70% relative atmospheric humidity for 7 days. Thereafter, the extent of rust fungus development on the leaves was determined.

In this test, the plants which had been treated with 16 ppm of the active ingredients I-7 and I-8 showed 0-25% infection, whereas the plants which had been treated with 16 ppm of the comparative active ingredients B.7, A.8, B.8, C.8 and D.8 were infected to 40-100% and the untreated plants were infected to 100%.

Use Example 2—Activity Against Net Blotch of Barley

Leaves of potted barley seedlings of the variety “Igri” were sprayed to runoff point with an aqueous preparation of active ingredient which had been prepared from a stock solution consisting of 10% of active ingredient, 63% of cyclohexanone and 27% of emulsifier. 24 hours after the spray coating had dried on, the leaves were inoculated with an aqueous spore suspension of Pyrenophora teres, the causative organism of net blotch. The test plants were subsequently placed in a greenhouse at 20-24° C. and 95-100% relative atmospheric humidity. After 6 days, the extent of the development of the disease was determined visually in % infection of the total leaf area.

In this test, the plants which had been treated with 63 ppm of the active ingredient I-7 showed 15% infection, whereas the plants which had been treated with 16 ppm of the comparative active ingredients A.7, B.7, C.7 and D.7 showed 25-100% infection, and the untreated plants showed 100% infection.

Use Example 3—Activity Against Botrytis cinerea on Bell Pepper Leaves

Bell pepper seedlings of the variety “Neusiedler Ideal Elite” were, after 4 to 5 leaves were well-developed, sprayed to runoff point with an aqueous preparation of active ingredient which had been prepared from a stock solution consisting of 10% of active ingredient, 63% of cyclohexanone and 27% of emulsifier. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea containing 1.7×10⁶ spores/ml in a 2% strength solution of Biomalz in water. The test plants were subsequently kept in a climatized chamber at 22-24° C. and high atmospheric humidity. After 5 days, the extent of the fungal infection on the leaves could be determined visually in %.

In this test, the plants which had been treated with 250 ppm of the active ingredient I-8, I-9 and I-11 showed 15-25% infection, whereas the plants which had been treated with 250 ppm of the comparative active ingredients A.8, B.8, C.8, D.8, A.9, B.9, D.9, A.11, B.11, C.11 and D.11 showed 40-100% infection, and the untreated plants showed 100% infection.

Examples of the Activity Against Animal Pests

The activity of the compounds of the general formula I against animal pests was demonstrated by the following experiments:

The active ingredients were formulated

a. as a 0.1% strength solution in acetone or b. as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight of Wettol® EM (nonionic emulsifier based on ethoxylated castor oil) and diluted to give the desired concentration, using acetone in the case of a. and water in the case of b.

After the experiments had been concluded, in each case the lowest concentration was determined at which the compounds still caused an 80-100% inhibition or mortality in comparison with untreated control experiments (limit or minimal concentration).

Example 1 Activity Against Nephotettix cincticeps (Green rice leafhopper), Contact Action

Filter disks (Ø 9 cm) were treated with 1 ml of the aqueous preparation of active ingredient and subsequently populated with five adult leafhoppers. The mortality was determined after 24 hours.

In this experiment, the active compound I-7 showed a limit concentration of 0.2 mg. 

We claim:
 1. A phenylcarbamate of the formula I

where: R¹ is C₁-C₄-alkyl; R² is cyano, nitro, trifluoromethyl, halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy; m is 0, 1 or 2, where the radicals R² may be different if m is 2; R³ is hydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl; R⁴, R⁶ independently of one another are each hydrogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₁₀-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₃-C₁₀-alkynylcarbonyl or C₁-C₁₀-alkylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the cyclic groups for their part may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkyloxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR⁷)—A_(n)—R⁸; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkyloxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR⁷)—A_(n)—R₈; R⁵ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, where the hydrocarbon radicals of these groups may be partially or fully halogenated or may carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C₁-C₄-alkoxy, arylthio, aryl-C₁-C₄-alkylthio, hetaryl, hetaryloxy, hetaryl-C₁-C₄-alkoxy, hetarylthio, hetaryl-C₁-C₄-alkylthio, where the cyclic radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR⁷)—A_(n)—R⁸; C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;  where A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C₁-C₆-alkyl; n is 0 or 1; R⁷ is hydrogen or C₁-C₆-alkyl and R⁸ is hydrogen or C₁-C₆-alkyl, and salts thereof.
 2. A compound of the formula I as claimed in claim 1 in which m is
 0. 3. A compound of the formula I as claimed in claim 1 in which R¹ is methyl.
 4. A compound of the formula I as claimed in claim 1 in which R³ is hydrogen, cyano, cyclopropyl, methyl, ethyl or 1-methylethyl.
 5. A compound of the formula I as claimed in claim 1 in which R⁴ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.
 6. A compound of the formula I as claimed in claim 1 in which R⁵ is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, unsubstituted or substituted aryl or hetaryl.
 7. A compound of the formula I as claimed in claim 1 in which R⁶ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, arylalkyl, hetarylalkyl, aryloxyalkyl or hetaryloxyalkyl.
 8. A process for preparing compounds of the formula I, which comprises reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III,

in which L¹ is a nucleophilically replaceable leaving group.
 9. A composition against animal pests or harmful fungi, comprising customary additives and an effective amount of a compound of the formula I as claimed in claim
 1. 10. A composition as claimed in claim 9 for controlling animal pests from the class of the insects, arachnids or nematodes. 